The instant invention provides C.sub.11 branched chain aldehydes and alcohols defined according to the generic structure: ##STR1## wherein one of X.sub.1 or X.sub.2 is hydrogen and the other of X.sub.1 or X.sub.2 is methyl; and wherein one of Z.sub.1 or Z.sub.2 is hydrogen and the other of Z.sub.1 or Z.sub.2 is hydroxymethyl having the structure: ##STR2## or carboxaldehyde having the structure: ##STR3## which are used to augment or enhance the aroma of perfume compositions, colognes or perfumed articles.
Inexpensive chemical compounds which can provide intense and long-lasting citrusy, green, melony, woody, peanut oil-like and vetiver-like aroma nuances are desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfumery compositions are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree, or they contribute undesirable or unwanted odor to the compositions.
C.sub.11 aliphatic aldehydes and alcohols are well known in the art of perfumery, e.g., n-undecanal and n-undecanol. Oxo reation products on hydrocarbon compounds are also well known in the perfumery industry. Thus, U.S. Pat. No. 4,145,505 discloses the formation of hydroxymethyl-formyl-tricyclo[5,2,1,0.sup.2,6 ]decane having the structure: ##STR4## wherein R.sub.1 and R.sub.2 are the hydroxymethyl group, CH.sub.2 OH or the formyl group CHO and R.sub.1 represents CH.sub.2 OH when R.sub.2 is CHO and vice versa. This polycyclic carboxaldehyde alcohol is indicated to be useful as a musk aroma imparting or augmenting material. The material is indicated to be produced by reaction of carbon monoxide and hydrogen with dicyclopentadiene. Other oxo reaction products on unsaturated hydrocarbons are known in the perfumery industry, for example, "Vandor-B", which is the oxo reaction product of carbon monoxide and hydrogen on diiosbutylene. This material has been produced by International Flavors & Fragrances Inc., the assignee of the instant patent application, for several years.
Nothing in the prior art discloses the use of the C.sub.11 aldehydes and alcohols produced by means of carrying out an "oxo" reaction (with carbon monoxide and hydrogen) on one or more diisoamylenes defined according to the generic structure: ##STR5## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent hydrogen or methyl with the proviso that (i) at least one of R.sub.1 and R.sub.2 represents methyl, (ii) at least one of R.sub.3 and R.sub.4 represents methyl, (iii) the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 is 3 and (iv) R.sub.1 and R.sub.2 represent hydrogen when R.sub.5 is methyl; to produce one or more of the compounds defined according to the structure: wherein one of X.sub.1 or X.sub.2 is hydrogen and the other of X.sub.1 or X.sub.2 is methyl; and wherein one of Z.sub.1 or Z.sub.2 is hydrogen and the other of Z.sub.1 or Z.sub.2 is hydroxymethyl having the structure: ##STR6## or carboxaldehyde having the structure: ##STR7##
"Diisoamylene" is indicated to be synthesized in the following references:
(i) Murphy & Lane, Ind. Eng. Chem., Prod. Res. Dev., Vol. 14, No. 3, 1975 p. 167 (Title: Oligomerization of 2-Methyl-2-Butene in Sulfuric Acid and Sulfuric-Phosphoric Acid Mixtures). PA1 (ii) Whitmore & Mosher, Vol. 68, J. Am. Chem. Soc., February, 1946, p. 281 (Title: The Depolymerization of 3,4,5,5-Tetramethyl-2-hexene and 3,5,5-Trimethyl-2-heptene in Relation to the Dimerization of Isoamylenes). PA1 (iii) Whitmore & Stahly, Vol. 67, J. Am. Chem. Soc., December, 1945, p. 2158 (Title: The Polymerization of Olefins. VIII The Depolymerization of Olefins in Relation to Intramolecular Rearrangements. II). PA1 (iv) U.S. Pat. No. 3,627,700, issued on Dec. 14, 1971, (Zuech). PA1 (v) U.S. Pat. No. 3,538,181, issued on Nov. 3, 1970 (Banks). PA1 (vi) U.S. Pat. No. 3,461,184, issued on Aug. 12, 1969 (Hay, et al). PA1 (vii) Gurwitsch, Chemische Berichte, 1912, Vol. 2, p. 796 (Production of Di-isoamylene from Isoamylene Using Mercury Acetate Catalyst).
United Kingdom Pat. No. 796,130 published on June 4, 1958 discloses the synthesis of polyalkylindanes by means of, interalia, reacting alpha-methylstyrene with trimethylethene (2-methyl-butene-2) in the presence of an acid catalyst such as, sulfuric acid or boron trifluoride etherate. It is further indicated that such compounds are useful intermediates in the production of perfumery compounds. Apparently, however, the more volatile diisoamylenes produced as side-products in the reaction of 2-methyl-butene-2 with alpha-methylstyrene have heretofore been discarded.
Catalytic oxo reactions on 10-carbon atom containing olefins are known to have been carried out according to "Organic Syntheses Via Methyl Carbonyls" Volume 2 by Wender and Pino (Wiley-1977) at Table 5, page 63, wherein it is indicated that the olefin having the structure: ##STR8## is reacted with carbon monoxide and hydrogen to produce a mixture of the three aldehydes having the structures: ##STR9## according to the reaction: ##STR10##
Chem. Abstracts, Volume 93, 1980, at 204066f discloses a summary of Japanese Kokai Tokkyo Koho 80-85,534 which discloses the reaction of diisobutylene with carbon monoxide in the presence of cobalt octacarbonyl, dioctylphosphine and dodecylbenzene at 120 kg/cm.sup.2 and 150.degree. C. for 5 hours yielding isononyl aldehyde and isononyl alcohol.
Nothing in the prior art, however, discloses the use of the oxo reaction product on diisoamylenes in augmenting or enhancing the aroma of perfume compositions, perfumed articles or colognes.